115377-59-8

Basic information

• Product Name: 1H-Imidazole-5-carboxamide, 4-(ethylamino)-1-(phenylmethyl)-
• CAS NO: 115377-59-8
• Molecular Formula: C13H16N4O
• Molecular Weight: 244.296
• Mol File: 115377-59-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-5-carboxamide, 4-(ethylamino)-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-5-carboxamide, 4-(ethylamino)-1-(phenylmethyl)-(115377-59-8)
• EPA Substance Registry System: 1H-Imidazole-5-carboxamide, 4-(ethylamino)-1-(phenylmethyl)-(115377-59-8)

Safety Data

• Hazardous Substances Data: 115377-59-8(Hazardous Substances Data)

Downstream Products

• 139927-97-2 7-Benzyl-3-ethyl-1-methyl-3,7-dihydro-purine-2,6-dione 
• 139927-84-7 7-benzyl-3-ethylxanthine 

Relevant articles and documents

Purines. XXX. Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis

On treatment with boiling 1 N aqueous NaOH for 2 h, 3,7-dialkyladenine salts (7: R1, R2= Me, Et, or PhCH2; X= Br, I, or ClO4) gave 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamides (8), 1-alkyl-4-amino-1H-imidazole-5-carboxamides (11), and N6,7-dialkyladenines (14) in 33-59 percent, 2-10 percent, and 2-5 percent yields, respectively.Under slightly milder reaction conditions, 3,7-dimethyladenine hydriodide (7a: X= I) afforded 1-methyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8a) together with 3,7-dimethylhypoxanthine (2a) as a by-product; 7-benzyl-3-methyladenine hydrobromide (7c: X= Br) furnished a small amount of 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamidine (5c) besides 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8c), 1-benzyl-4-amino-1H-imidazole-5-carboxamide (11c), and 7-benzyl-N6-methyladenine (14c).These results are best interpreted in terms of pathways involving hydrolytic deamination, ring fission in the pyrimidine and imidazole moieties, cyclization, and Dimroth rearrangement.The instability of 7a (X= I) in aqueous alkali was compared with that of the four possible Nx,9-dimethyl isomers, and the relative ease with which the adenine ring underwent hydrolytic ring fission was found to decrease in the order 3,9- (17) >7,9- (18) >1,9- (19) >3,7- (7a) >>N6,9-dimethyl isomer (20).Keywords - 3,7-dialkyladenine alkaline hydrolysis; ring fission; deamination; rearrangement; 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamide; 1-alkyl-4-amino-1H-imidazole-5-carboxamide; N6,7-dialkyladenine